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Aryl imidazoline compounds and their preparation methods and uses

A technology of aryl imidazoline and imidazoline, which is applied in the field of pesticides, can solve the problems of less research on the antibacterial activity of pesticides and no reports on the antibacterial activity of imidazoline compounds, and achieve good antibacterial activity, simple synthesis method, and cheap synthetic materials Easy to get effect

Active Publication Date: 2020-07-10
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In summary, there have been many studies on the anti-analgesic, anti-serotonin, anti-arrhythmic and anti-inflammatory activities of imidazoline compounds, but there are relatively few studies on their antibacterial activities of pesticides. The research on the antibacterial activity of 1,2,4-trisubstituted imidazoline compounds is hardly reported

Method used

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  • Aryl imidazoline compounds and their preparation methods and uses
  • Aryl imidazoline compounds and their preparation methods and uses
  • Aryl imidazoline compounds and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Example 1: Synthesis of 1-(2-hydroxybenzyl)-2-(3-nitrophenyl)-3-(4-methoxyphenyl)imidazoline.

[0129] Weigh N-(4-methoxyphenyl)-N'-(2-hydroxyphenyl)ethylenediamine 0.280g (1mmol), 3-nitrobenzaldehyde 0.212g (1.4mmol), La(SO 3 CF 3 ) 3 0.059g (0.10mmol) and 0.25g powder molecular sieve into a 100mL three-necked flask, and then add 30mL CHCl 3 Mixed solvent with cyclohexane (V:V=1:4), feed N 2 protective gas. Heated to 80°C and refluxed for 3h, and desolvated under reduced pressure after the reaction was complete. Extract with ethyl acetate (50mL×3 times), combine the organic layers, wash with distilled water (40mL×3) and saturated NaCl solution (40mL×3) successively, and then wash with saturated NaHSO 3 solution (40mL×3) was washed to remove excess aldehyde, and then washed with anhydrous Na 2 SO 4 The organic phase was dried, filtered with suction, precipitated under reduced pressure and subjected to column chromatography to obtain a red solid, melting point:...

Embodiment 2

[0131] Example 2: Synthesis of 1-(2-hydroxybenzyl)-2-(2-nitrophenyl)-3-(4-methoxyphenyl)imidazoline.

[0132] Weigh N-(4-methoxyphenyl)-N'-(2-hydroxyphenyl)ethylenediamine 0.276g (1mmol), 2-nitrobenzaldehyde 0.213g (1.4mmol), La(SO 3 CF 3 ) 3 0.059g (0.10mmol) and 0.25g powder molecular sieve into a 100mL three-necked flask, and then add 30mL CHCl 3 , into the helium protective gas. Heated to 85°C and refluxed for 1h, and desolvated under reduced pressure after the reaction was complete. Extract with ethyl acetate (50mL×3 times), combine the organic layers, wash with distilled water (40mL×3) and saturated NaCl solution (40mL×3) successively, and then wash with saturated NaHSO 3 solution (40mL×3) was washed to remove excess aldehyde, and then washed with anhydrous Na 2 SO 4 The organic phase was dried, filtered with suction, precipitated under reduced pressure and subjected to column chromatography to obtain a red solid with a melting point (mp): 143.1-143.3° C. and a ...

Embodiment example 3

[0134] Example 3: Synthesis of 1-(2-hydroxybenzyl)-2-(4-nitrophenyl)-3-(3-tolyl)imidazoline.

[0135] Weigh N-(3-methylphenyl)-N'-(2-hydroxyphenyl)ethylenediamine 0.256g (1mmol), 4-nitrobenzaldehyde 0.214g (1.4mmol), La(SO 3 CF 3 ) 3 0.059g (0.10mmol) and 0.25g powder molecular sieve into a 100mL three-necked flask, then add 30mL tetrahydrofuran, and pass through N 2 protective gas. Heated to 90°C and refluxed for 8h, and desolvated under reduced pressure after the reaction was complete. Extract with ethyl acetate (50mL×3 times), combine the organic layers, wash with distilled water (40mL×3) and saturated NaCl solution (40mL×3) successively, and then wash with saturated NaHSO 3 solution (40mL×3) was washed to remove excess aldehyde, and then washed with anhydrous Na 2 SO 4 The organic phase was dried, filtered with suction, and precipitated under reduced pressure to obtain an orange solid by column chromatography, melting point (mp): 162.5-163.5°C, yield: 79.7%.

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Abstract

The invention discloses a 1-(2-hydroxybenzyl)-2-(alkyl or nitrophenyl)-3-aryl imidazoline compound with a general formula (I). In the formula (I), R<1> is C1-C2 alkyl phenyl or C1-C2 alkoxy phenyl; and R<2> is nitrophenyl or C1-C4 alkyl. The compound has good bactericidal activity on pathogenic bacteria in crops. (The formula (I) is shown in the description).

Description

technical field [0001] The present invention relates to an aryl imidazoline compound, in particular to a 1-(2-hydroxybenzyl)-2-(alkyl or nitrophenyl)-3-aryl imidazoline compound with fungicidal activity Its preparation method and bactericidal application belong to the technical field of pesticides. Background technique [0002] Imidazoline is an important representative of nitrogen-containing heterocyclic compounds. The nitrogen atom on the core diaza five-membered ring has a lone pair of electrons, which is a better electron donor, which endows this type of compound with chemical and biological properties. of significance. In 2001, Matosiuk et al. reported the synthesis and physicochemical properties of new carbonyl derivatives of 1-aryl-2-iminoimidazolidine, and found that they had analgesic effects on the central nervous system (CNS) of animals, and the urea moiety contained 1-aryl-2-iminoimidazolidine derivatives have good affinity to opioid (μ) and serotonin (5-HT2). ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/02C07D405/04A01N43/50A01P3/00
CPCA01N43/50C07D233/02C07D405/04
Inventor 唐子龙姚园代宁宁汪明万义超焦银春彭丽芬张少伟
Owner HUNAN UNIV OF SCI & TECH
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